1,1'-Carbonyldiimidazole → N-Methoxy-N-methyl-1H-indazole-3-carboxamide

HRID 218458

反応式

HRID 218458 の反応式
[C:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][N:5]=1)(O)=[O:2].C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[CH3:26][NH:27][O:28][CH3:29]>CN(C=O)C>[CH3:29][O:28][N:27]([CH3:26])[C:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][N:5]=1)=[O:2]

参加物

5

反応物 3

HCID 682631,1'-CarbonyldiimidazoleHCID 78250Indazole-3-carboxylic acidHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

生成物 1

HCID 16036867N-Methoxy-N-methyl-1H-indazole-3-carboxamide収率 81.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
65 °C

実験手順

3-Carboxyindazole (10 g, 61.7 mmol) in DMF (100 mL) was treated with carbonyldiimidazole (11 g, 67.84 mmol) at rt with gas evolution for 15 min, after which the reaction mixture was heated up to 65° C. for 2 hours. After cooling to rt, N,O-dimethylhydroxyamine-HCl (4.14 g, 67.8 mmol) was added and the mixture was heated to 65° C. overnight. The reaction was cooled, quenched with water, extracted with CH2Cl2 and washed with water. The combined organic phase was dried and concentrated to afford N-methoxy-N-methyl-1H-indazole-3-carboxamide (10.3 g, 81.4%).

後処理

  1. temperatureAfter cooling to rt
  2. temperaturethe mixture was heated to 65° C. overnight
  3. temperatureThe reaction was cooled
  4. customquenched with water
  5. extractionextracted with CH2Cl2
  6. washwashed with water
  7. customThe combined organic phase was dried
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-c678d9ae3a624567bfad52efe9f10168
出典データセット
uspto-grants-2012_06
特許番号
US08198456B2

関連ノート

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